Benzene → Benzyl 9-oxo-3-azaspiro(5.5)undec-7-ene-3-carboxylate

HRID 62217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62217
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1.[CH3:37][C:38](=[O:41])[CH:39]=[CH2:40]>>[O:41]=[C:38]1[CH2:39][CH2:40][C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)[CH:1]=[CH:37]1

Komponenten

5

Edukt 4

HCID 241BenzeneHCID 6570Methyl vinyl ketoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

Produkt 1

HCID 23435732Benzyl 9-oxo-3-azaspiro(5.5)undec-7-ene-3-carboxylateAusbeute 57,2 %

Versuchsvorschrift

Benzyl 4-formylpiperidine-1-carboxylate (5.17 g, 20.907 mmol) and p-Toluenesulfonic acid monohydrate (0.398 g, 2.091 mmol) were stirred in Benzene (30.0 ml, 334.136 mmol) at 70° C. But-3-en-2-one (3.76 ml, 41.813 mmol) was added and the reaction mixture was refluxed o/n while removing water with dean-stark trap. After cooling the reaction mixture to rt, sat. NaHCO3 soln. was added and the organic layer was dried over Na2SO4 and evaporated. The resulting oil was purified by Biotage (SiO2, 250 g, EtOAc/Hep 10% to 50%) to afford the title compound (3.58 g, 11.96 mmol, 57.2% yield).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed o/n
  2. customwhile removing water with dean-stark trap
  3. additionwas added
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customevaporated
  6. customThe resulting oil was purified by Biotage (SiO2, 250 g, EtOAc/Hep 10% to 50%)

Quellen und Nachweise

ORD-Eintrag
ord-7f02d74748974695a9ee031a838a2b47
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446046B2

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